Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version
Viewed by 52 travelers

Exploring the Midwest: Wisconsin, Chicago, and New York

Thursday, August 17, 2023

6:00 AM: Departure from Home

Start your adventure by departing from your home and heading towards Wisconsin. Take a flight or drive to reach your first destination.

10:00 AM: Milwaukee, Wisconsin

Arrive in Milwaukee, Wisconsin, and kickstart your day with a visit to the Milwaukee Art Museum. Explore the diverse collection of paintings, sculptures, and decorative arts in this architectural marvel designed by Santiago Calatrava.

Cost Estimate: Admission to the museum - $15 per person

Time Spent: 2-3 hours

1:00 PM: Chicago, Illinois

Travel to Chicago, Illinois, and savor an iconic deep-dish pizza at Giordano's. Indulge your taste buds with this Chicago specialty and experience the city's unique culinary culture.

Cost Estimate: Deep-dish pizza at Giordano's - $20 per person

Time Spent: 1-2 hours

3:00 PM: Millennium Park, Chicago

Head to Millennium Park, a popular urban oasis in the heart of downtown Chicago. Take a leisurely stroll through the park, marvel at Cloud Gate (The Bean), and enjoy the Crown Fountain.

Cost Estimate: Free admission

Time Spent: 1-2 hours

5:00 PM: The Magnificent Mile, Chicago

Treat yourself to some retail therapy on The Magnificent Mile, Chicago's premier shopping destination. Explore the high-end stores, boutiques, and iconic department stores along this vibrant stretch of Michigan Avenue.

Cost Estimate: Varies depending on personal shopping preferences

Time Spent: 2-3 hours

8:00 PM: Departure to New York

Say goodbye to Chicago and board a flight or take a train to your final destination, New York City.

Hidden Gems and Local Favorites

When in Chicago, don't miss the chance to explore some of its hidden gems and local favorites. Venture out to neighborhoods like Wicker Park, known for its vibrant street art, trendy boutiques, and lively nightlife. Enjoy cocktails at Violet Hour, a speakeasy-style bar with a retro ambiance. For a more relaxed experience, visit the Garfield Park Conservatory, a stunning botanical garden filled with lush greenery and beautiful plant displays.

For more information on hotel and flight prices, you can check here.

0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version